Painless1099: An ACe in the Hole for freelancers

Calling all independent contractors: ACe wants YOu.

Freelancers and independent contractors are great at what they do and, usually, bad at doing the taxes that come with it. There is no W2 withholding for the 1099 workforce and most don’t know—roughly 70% to be exact—the details and rules of taxes that accompany the nature of their work. Of those who are well aware, saving can still be a struggle.

That’s where ACe Callwood and the Painless1099 team come in. The self-proclaimed “sexiest tax guys in the cohort of 43North 2015 winners” want to help you. Painless1099 uses a smart bank account with an algorithm that separates out your income into what needs to be saved for Uncle Sam and what is safe to spend. Whether you have yet to learn about the rules waiting to ruin your April 15th, or you’re not gifted with the willpower to save money (no judgment, I’m with you), Painless1099 makes your life exponentially easier.


As an entrepreneur who founded three companies prior to landing on Painless1099, ACe and his team are no strangers to this pain. In fact, the idea for Painless1099 came when product architect Matt Russo was slammed with a casual $15,000 bill from the IRS at year’s end as a result of improperly allocating his paychecks. He gets it.

With the help of ACe and the guys who have been there, you’re in good hands. It’s a pretty sweet deal for you.


For a better (and funnier) description of all that they do, check out their video starring ACe and Matt themselves. I mean, come on, who wouldn’t want these guys taking care of their taxes?